Phosphazene compound comprising cyano group, preparation method and uses thereof

Abstract

The present invention relates to a phosphazene compound comprising cyano group having a molecular structure of Formula (I); wherein, Y and Y′ are independently selected from organic groups; M 1 and M 2 are independently selected from phosphazene groups, and M 1 contains m 1 phosphorus atoms, and M 2 contains m 2 phosphorus atoms; X 1 , X 1 ′, X 2 , X 3 and X 4 are independently selected from any one of the sixth main-group elements; R and R′ are independently selected from divalent organic groups; a is an integer greater than or equal to 0; b is an integer greater than or equal to 1; and c is an integer greater than or equal to 0; and a+b=2m 1 , d+2=2m 2 . The present invention achieves a synergistic effect with P and N of phosphazene group by introducing cyano group to the phosphazene group, and thus improves thermal stability and flame retardancy of the phosphazene compound, and the compatibility thereof with other components is excellent. The resin composition comprising the phosphazene compound of the present invention has good heat resistance, water resistance, adhesive properties and mechanical properties, and thus the application thereof is widened.

1 . A phosphazene compound comprising cyano group, having a molecular structure as shown in Formula (I): 
       
         
           
           
               
               
           
         
       
       wherein, Y and Y′ are independently selected from organic groups;
 M 1  and M 2  are independently selected from phosphazene groups, and M 1  contains m 1  phosphorus atoms, and M 2  contains m 2  phosphorus atoms; 
 X 1 , X 1 ′, X 2 , X 3  and X 4  are independently selected from any one of the sixth main-group elements; 
 R and R′ are independently selected from divalent organic groups; 
 a is an integer greater than or equal to 0; b is an integer greater than or equal to 1; and c is an integer greater than or equal to 0; and a+b=2m 1 , d+2=2m 2 . 
 
     
     
         2 . The phosphazene compound of  claim 1 , wherein M 1  and M 2  are independently selected from cyclic phosphazene having a structure of Formula (II) or linear phosphazene having a structure of Formula (III); 
       
         
           
           
               
               
           
         
       
       in Formula (II) or Formula (III), n 1  is an integer greater than or equal to 2, and n 2  is an integer greater than or equal to 1. 
     
     
         3 . The phosphazene compound of  claim 1 , wherein M 1  and M 2  are any one of cyclotriphosphazene, cyclotetraphosphazene or non-cyclic polyphosphazene, or a combination of at least two of them. 
     
     
         4 . The phosphazene compound of  claim 1 , wherein Y and Y′ are independently selected from the group consisting of substituted or unsubstituted straight chain alkyl, substituted or unsubstituted branched alkyl, or substituted or unsubstituted aryl. 
     
     
         5 . The phosphazene compound of  claim 1 , wherein Y and Y′ are independently selected from the group consisting of C 1 -C 30  substituted or unsubstituted straight chain alkyl, C 1 -C 30  substituted or unsubstituted branched alkyl, or C 6 -C 30  substituted or unsubstituted aryl. 
     
     
         6 . The phosphazene compound of  claim 1 , wherein Y and Y′ are independently selected from the group consisting of phenyl, tolyl, xylyl, ethylphenyl, methyl, ethyl, n-propyl, n-butyl, isopropyl, or isobutyl. 
     
     
         7 . The phosphazene compound of  claim 1 , wherein Y and Y′ are independently phenyl, tolyl, xylyl or ethylphenyl. 
     
     
         8 . The phosphazene compound of  claim 1 , wherein R and R′ are independently selected from the group consisting of substituted or unsubstituted straight chain alkylene, substituted or unsubstituted branched alkylene, and substituted or unsubstituted arylene. 
     
     
         9 . The phosphazene compound of  claim 1 , wherein R and R′ are independently selected from the group consisting of C 1 -C 30  substituted or unsubstituted straight chain alkylene, C 1 -C 30  substituted or unsubstituted branched alkylene, and C 6 -C 30  substituted or unsubstituted arylene. 
     
     
         10 . The phosphazene compound of  claim 1 , wherein R and R′ are independently selected from the group consisting of phenylene, methylphenylene, dimethylphenylene, ethylphenylene, 
       
         
           
           
               
               
           
         
       
       methylene, ethylene, propylene, 
       
         
           
           
               
               
           
         
       
       n-butylene, or isopropylene. 
     
     
         11 . The phosphazene compound of  claim 1 , wherein R and R′ are independently phenylene, methylphenylene, dimethylphenylene, ethylphenylene, or 
       
         
           
           
               
               
           
         
       
     
     
         12 . The phosphazene compound of  claim 1 , wherein each X 1 , X 1 ′, X 2 , X 3  and X 4  is O. 
     
     
         13 . The phosphazene compound of  claim 1 , wherein the phosphazene compound is selected from 
       
         
           
           
               
               
           
         
       
       wherein each M 1 , M 2 , a, b, R and R′ has the same selection scopes as that in  claim 1 . 
     
     
         14 . The phosphazene compound of  claim 1 , wherein the phosphazene compound is selected from the group consisting of 
       
         
           
           
               
               
           
         
       
       wherein each M 1 , M 2 , a and b has the same selection scopes as that in  claim 1 . 
     
     
         15 . The phosphazene compound of  claim 1 , wherein the phosphazene compound is selected from 
       
         
           
           
               
               
           
         
       
     
     
         16 . A method for preparing the phosphazene compound comprising cyano group of  claim 1 , comprising the step of carrying out a nucleophilic substitution reaction of phosphazene chloride and a first raw material compound; 
       the phosphazene chloride is M 1 (Cl) p  and/or M 2 (Cl) q , p=2m 1 , and q=2m 2 ; 
       the first raw material compound is any one of Y—X 1 —H, Y′—X 1 ′—H, H—X 2 —R—CN or H—X 4 —R′—X 3 —H, or a combination of at least two of them; the first raw material compound must comprise H—X 2 —R—CN or H—X 4 —R′—X 3 —H; wherein, each X 1 , X 1 ′, X 2 , X 3 , X 4 , Y, R and R′ has the same meaning as that in  claim 1 , and R and Y are substituted or unsubstituted phenyl. 
     
     
         17 . A prepreg prepared by impregnating a substrate with a cyanate ester resin composition comprising the phosphazene compound of  claim 1  or coating an cyanate ester resin composition comprising the phosphazene compound of  claim 1  onto a substrate. 
     
     
         18 . The prepreg of  claim 17 , wherein the substrate is a glass fiber substrate, a polyester substrate, a polyimide substrate, a ceramic substrate or a carbon fiber substrate.